methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

Base Information

• Chemical Name: methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate
• CAS No.: 905281-17-6
• Molecular Formula: C₁₉H₁₈BrNO₄
• Molecular Weight: 404.26
• Mol file: 905281-17-6.mol

Synonyms:methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

Chemical Property of methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

There total 3 articles about methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

3-methyl-4-bromobenzaldehyde (78775-11-8) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate (905281-17-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jm0600904

Reference yield:

4-Bromo-3-methylbenzoic acid methyl ester (148547-19-7) → methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate (905281-17-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / lithium tetrahydroborate / tetrahydrofuran / 48 h / 25 °C

2: 96 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 2 h / -78 - 20 °C

3: 85 percent / 1,8-diazabicyclo[5.4.0]-undec-7-ene / CH₂Cl₂ / 1.5 h / 20 °C

With lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;

DOI:10.1021/jm0600904

Reference yield:

4-bromo-3-methylbenzylalcohol (149104-89-2) → methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate (905281-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 2 h / -78 - 20 °C

2: 85 percent / 1,8-diazabicyclo[5.4.0]-undec-7-ene / CH₂Cl₂ / 1.5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; 1: Swern oxidation;

DOI:10.1021/jm0600904

upstream raw materials:

3-methyl-4-bromobenzaldehyde

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

4-Bromo-3-methylbenzoic acid methyl ester

4-bromo-3-methylbenzylalcohol

Downstream raw materials:

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)propanoate

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate